EP4287339A1 - Électrolyte non aqueux pour batterie secondaire au lithium et batterie secondaire au lithium le comprenant - Google Patents

Électrolyte non aqueux pour batterie secondaire au lithium et batterie secondaire au lithium le comprenant Download PDF

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Publication number
EP4287339A1
EP4287339A1 EP22881277.2A EP22881277A EP4287339A1 EP 4287339 A1 EP4287339 A1 EP 4287339A1 EP 22881277 A EP22881277 A EP 22881277A EP 4287339 A1 EP4287339 A1 EP 4287339A1
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EP
European Patent Office
Prior art keywords
secondary battery
lithium secondary
electrolyte solution
aqueous electrolyte
lithium
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EP22881277.2A
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German (de)
English (en)
Inventor
Jun Hyeok Han
Kyoung Ho Ahn
Won Kyung SHIN
Chul Haeng Lee
Won Tae Lee
Su Hyeon Ji
Young Ho Oh
You Kyeong Jeong
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LG Energy Solution Ltd
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LG Energy Solution Ltd
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Priority claimed from KR1020220127418A external-priority patent/KR102522492B1/ko
Application filed by LG Energy Solution Ltd filed Critical LG Energy Solution Ltd
Publication of EP4287339A1 publication Critical patent/EP4287339A1/fr
Pending legal-status Critical Current

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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0568—Liquid materials characterised by the solutes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0569—Liquid materials characterised by the solvents
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0028—Organic electrolyte characterised by the solvent
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0025—Organic electrolyte
    • H01M2300/0028—Organic electrolyte characterised by the solvent
    • H01M2300/0037—Mixture of solvents
    • H01M2300/0042—Four or more solvents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Definitions

  • the present invention relates to anon-aqueous electrolyte solution for a lithium secondary battery, comprising an additive which may form a robust SEI film, and a lithium secondary battery capable of suppressing an increase in initial resistance and improving output characteristics by including the same.
  • a secondary battery is a technology that is most suitable for various applications among developed technologies, and among the secondary batteries, a lithium ion battery, which may be miniaturized to be applicable to a personal IT device and has the highest energy density, is in the spotlight.
  • a lithium ion battery is composed of a positive electrode comprised of a transition metal oxide containing lithium, a negative electrode comprised of a carbon-based material such as graphite capable of storing lithium, an electrolyte solution that is a medium for transferring lithium ions, and a separator. It is important to properly select these components in order to improve the electrochemical properties of the battery.
  • PF6- anions are thermally decomposed from lithium salts such as LiPF6 contained in an electrolyte solution to form Lewis acids such as PF5, which react with moisture to generate HF.
  • Materials such as PF5 or HF may not only destruct a film formed on the surface of an electrode, but also cause decomposition of an organic solvent.
  • PF5 or HF may not only destruct a film formed on the surface of an electrode, but also cause decomposition of an organic solvent.
  • a side reaction between the exposed surface of the electrode and the electrolyte solution causes the elution of transition metal ions from the positive electrode.
  • the transition metal ions of the positive electrode are eluted, the lattice structure of the positive electrode becomes unstable, which leads to the generation of active oxygen in the positive electrode.
  • the present invention aims to provide a non-aqueous electrolyte solution for a lithium secondary battery including an additive capable of providing a SEI enhancing effect, and a lithium secondary battery with improved output characteristics and a suppressed increase in battery resistance by including the same.
  • a non-aqueous electrolyte solution for a lithium secondary battery which comprises a lithium salt, a non-aqueous organic solvent and a compound represented by the following Formula 1.
  • R 1 and R 2 are each independently an alkylene group having 1 to 10 carbon atoms
  • R 3 is an alkyl group having 1 to 20 carbon atoms which are substituted with one or more fluorines.
  • a lithium secondary battery which includes a positive electrode including a positive electrode active material; a negative electrode including a negative electrode active material; a separator disposed between the negative electrode and the positive electrode; and the non-aqueous electrolyte solution for a lithium secondary battery according to the present invention.
  • the compound represented by Formula 1 included in the non-aqueous electrolyte for a lithium secondary battery of the present invention includes a propargyl group (-C ⁇ C-) and a fluorocarbon functional group substituted with one or more fluorine elements in the structure, it may be reduced before the organic solvent to form a low-resistance SEI film including a fluorocarbon component on the surface of the electrode, thereby suppressing additional reductive decomposition of the non-aqueous electrolyte solution.
  • the expressions "a” and “b” in the description of "a to b carbon atoms” in the specification each denote the number of carbon atoms included in a specific functional group. That is, the functional group may include “a” to "b” carbon atoms.
  • substitution denotes that at least one hydrogen bonded to carbon is substituted with an element other than hydrogen, for example, an alkyl group having 1 to 5 carbon atoms or a fluorine element.
  • a film having passivation ability is formed on surfaces of a negative electrode and a positive electrode, while a non-aqueous electrolyte solution is decomposed during initial charge and discharge, to secure high-temperature storage characteristics.
  • the film is deteriorated by Lewis acid materials such as HF and PF 5 generated by thermal decomposition of lithium salts (LiPF 6 , etc.) widely used in lithium ion batteries.
  • the surface resistance of the electrode increases due to a change in the structure of the surface, and the theoretical capacity decreases as the metallic elements, which are the redox center, are lost, and thus expressing capacity may be reduced.
  • the transition metal ions thus eluted are not only electrodeposited on the negative electrode reacting in a strong reduction potential range to consume electrons, but also destruct a film during electrodeposition to expose the surface of the negative electrode, which causes an additional electrolyte decomposition reaction. As a result, negative electrode resistance and irreversible capacity increase, thereby resulting in a continuous degradation of cell output characteristics.
  • the present invention aims at providing a non-aqueous electrolyte solution for a lithium secondary battery capable of forming a low-resistance SEI film by including a compound comprising a propargyl group (-C ⁇ C-) and a fluorocarbon functional group substituted with one or more fluorine elements in the molecular structure as an additive, and a lithium secondary battery including the same.
  • the present invention provides a non-aqueous electrolyte solution for a lithium secondary battery including a lithium salt, a non-aqueous organic solvent and a compound represented by Formula 1 below.
  • R 1 and R 2 are each independently an alkylene group having 1 to 10 carbon atoms
  • R 3 is an alkyl group having 1 to 20 carbon atoms substituted with one or more fluorines.
  • any lithium salt typically used in an electrolyte solution for a lithium secondary battery may be used as the lithium salt without limitation, and, for example, the lithium salt may include Li + as a cation, and may include at least one selected from the group consisting of F - , Cl - , Br - , I - , NO 3 - , N(CN) 2 - , BF 4 - , ClO 4 -, AlO 4 - , AlCl 4 - , PF 6 - , SbF 6 - , AsF 6 - , B 10 Cl 10 - , BF 2 C 2 O 4 - , BC 4 O 8 - , PF 4 C 2 O 4 - , PF 2 C 4 O 8 - , (CF 3 ) 2 PF 4 - , (CF 3 ) 3 PF 3 - , (CF 3 ) 4 PF
  • the lithium salt may include at least one selected from the group consisting of LiCl, LiBr, LiI, LiBF 4 , LiClO 4 , LiAlO 4 , LiAlCl 4 , LiPF 6 , LiSbF 6 , LiAsF 6 , LiB 10 Cl 10 , LiBOB (LiB(C 2 O 4 ) 2 ), LiCF 3 SO 3 , LiTFSI (LiN(SO 2 CF 3 ) 2 ), LiFSI (LiN(SO 2 F) 2 ), LiCH 3 SO 3 , LiCF 3 CO 2 , LiCH 3 CO 2 and LiBETI (LiN (SO 2 CF 2 CF 3 ) 2 ) as an anion.
  • the lithium salt may include a single material selected from the group consisting of LiBF 4 , LiClO 4 , LiPF 6 , LiBOB (LiB(C 2 O 4 ) 2 ), LiCF 3 SO 3 , LiTFSI (LiN(SO 2 CF 3 ) 2 ), LiFSI (LiN(SO 2 F) 2 ) and LiBETI (LiN(SO 2 CF 2 CF 3 ) 2 ), or a mixture of two or more thereof. More specifically, the lithium salt may includeLiPF 6 .
  • the lithium salt may be appropriately changed in a normally usable range, but may be present in a concentration of 0.8 M to 3.0 M, specifically, 1.0 M to 3.0 M in the electrolyte solution to obtain an optimum effect of forming a film for preventing corrosion of a surface of an electrode.
  • viscosity of the non-aqueous electrolyte solution may be controlled so that optimum impregnability may be achieved, and an effect of improving capacity characteristics and cycle characteristics of the lithium secondary battery may be obtained by improving mobility of lithium ions.
  • the non-aqueous organic solvent may include at least one selected from a cyclic carbonate compound, a linear carbonate compound, and a linear ester compound.
  • the cyclic carbonate compound is a highly viscous organic solvent which may well dissociate the lithium salt in a non-aqueous electrolyte solution due to high permittivity, wherein specific examples thereof may be at least one organic solvent selected from the group consisting of ethylene carbonate (EC),propylene carbonate (PC), 1,2-butylene carbonate, 2,3-butylene carbonate, 1,2-pentylene carbonate, 2,3-pentylene carbonate, and vinylene carbonate, and, among them, may include at least one of ethylene carbonate and propylene carbonate (PC).
  • EC ethylene carbonate
  • PC propylene carbonate
  • PC propylene carbonate
  • the linear carbonate compound is an organic solvent having low viscosity and low permittivity, wherein typical examples thereof may be at least one organic solvent selected from the group consisting of dimethyl carbonate (DMC),diethyl carbonate (DEC),dipropyl carbonate, ethylmethyl carbonate (EMC), methylpropyl carbonate, and ethylpropyl carbonate, and specifically may include ethylmethyl carbonate (EMC).
  • DMC dimethyl carbonate
  • DEC diethyl carbonate
  • EMC ethylmethyl carbonate
  • EMC ethylmethyl carbonate
  • methylpropyl carbonate methylpropyl carbonate
  • ethylpropyl carbonate methylpropyl carbonate
  • EMC ethylmethyl carbonate
  • linear ester compound may be one selected from the group consisting of methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate, propyl propionate and butyl propionate, and may typically include at least one of ethyl propionate and propyl propionate.
  • a mixed solvent of a cyclic carbonate compound, a linear carbonate compound, and a linear ester compound may be used as the non-aqueous organic solvent.
  • the cyclic carbonate compound may be included in an amount of 50 vol% or less specifically 40 vol% or less, preferably 30 vol% or less, based on the total content of the non-aqueous organic solvent of the present invention.
  • the non-aqueous organic solvent may further include at least one of a cyclic ester compound, an ether-based compound, an amide-based compound and a nitrile-based compound.
  • the cyclic ester compound may be at least one selected from the group consisting of ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -valerolactone, and ⁇ -caprolactone.
  • any one selected from the group consisting of dimethyl ether, diethyl ether, dipropyl ether, methylethyl ether, methylpropyl ether and ethylpropyl ether or a mixture of two or more of these may be used as the ester-based compound.
  • the nitrile-based compound may be at least one selected from the group consisting of acetonitrile, propionitrile, butyronitrile, valeronitrile, caprylonitrile, heptanenitrile, cyclopentane carbonitrile, cyclohexane carbonitrile, 2-fluorobenzonitrile, 4-fluorobenzonitrile, difluorobenzonitrile, trifluorobenzonitrile, phenylacetonitrile, 2-fluorophenylacetonitrile,and 4-fluorophenylacetonitrile.
  • the remainder excluding the lithium salt and additive in the non-aqueous electrolyte solution of the present invention may all be non-aqueous organic solvents unless otherwise stated.
  • the non-aqueous electrolyte solution for a lithium secondary battery of the present invention may include a compound represented by the following Formula 1 as an electrolyte solution additive.
  • R 1 and R 2 are each independently an alkylene group having 1 to 10 carbon atoms; and R 3 is an alkyl group having 1 to 20 carbon atoms which are substituted with one or more fluorines.
  • the compound represented by Formula 1 includes a propargyl functional group in its structure and is easily reduced and decomposed on the surface of the negative electrode to form an SEI film having low resistance and high passivation ability. Accordingly, the durability of the negative electrode itself may be improved, but the transition metals may be prevented from being electrodeposited on the surface of the negative electrode, thereby preventing the self-discharge reaction of graphite-based and silicon-based negative electrodes due to the additional reduction and decomposition reaction of the electrolyte solution caused by the instability of the SEI film.
  • the compound represented by Formula 1 forms a film which has secured oxidation resistance on the surface of the positive electrode by including a fluorocarbon functional group in which one or more fluorine elements are substituted at the end of the structure to suppress the elution of metallic impurities from the positive electrode and suppress the eluted metal ions from being electrodeposited and precipitated on the negative electrode, thereby preventing an internal short circuit.
  • the non-aqueous electrolyte solution of the present invention includes a compound represented by Formula 1 including a fluorocarbon functional group substituted with one or more fluorine elements and propargyl group having excellent flame retardancy and non-flammability as an additive to form a robust SEI film having low resistance, thereby suppressing additional reductive decomposition of the non-aqueous electrolyte solution, but also preventing the self-discharge reaction of the negative electrode.
  • a lithium secondary battery that suppresses an increase in initial resistance and has improved room temperature and low-temperature output characteristics may be manufactured.
  • R 1 and R 2 may each independently be an alkylene group having 1 to 5 carbon atoms
  • R 3 may be an alkyl group having 3 to 20 carbon atoms substituted with one or more fluorines.
  • R 1 and R 2 may each independently be an alkylene group having 1 to 3 carbon atoms, and R 3 may be an alkyl group having 3 to 15 carbon atoms substituted with one or more fluorines.
  • R 3 may be an alkyl group having 3 to 10 carbon atoms substituted with one or more fluorines.
  • the compound represented by Formula 1 may be at least one of the compounds represented by the following Formula 1a to Formula 1c.
  • the compound represented by Formula 1 may be included in an amount of 0.01 wt% to 10.0 wt% based on the total weight of the non-aqueous electrolyte solution for a lithium secondary battery.
  • a low-resistance SEI film is formed on the surface of the negative electrode, while minimizing disadvantages such as side reactions, capacity degradation and resistance increase caused by additives, which may improve the effect of transferring the lithium.
  • the self-discharge reaction of the negative electrode may be prevented by suppressing the additional reduction decomposition reaction of the electrolyte solution.
  • a stable film is formed during the operation of the battery.
  • viscosity of the non-aqueous electrolyte solution may be controlled so that optimum impregnability may be achieved, an increase in battery resistance due to the decomposition of additives may be effectively suppressed, and the ionic conductivity in the battery may be also further increased to prevent the degradation of output characteristics.
  • the compound represented by Formula 1 may be included in an amount of 0.1 wt% to 6.0 wt%, specifically 0.5 wt% to 5 wt%, preferably 0.5 wt% to 3 wt% in the non-aqueous electrolyte solution.
  • the non-aqueous electrolyte solution for a lithium secondary battery of the present invention may further include other additional additives in addition to the compound represented by Formula 1, if necessary, in order to prevent the collapse of the negative electrode from occurring due to the decomposition of the non-aqueous electrolyte solution in a high power environment or to further improve low-temperature high rate discharge characteristics, high-temperature stability, overcharge prevention, and an effect of suppressing battery swelling at high temperatures.
  • Examples of the other additive may be at least one selected from the group consisting of a cyclic carbonate-based compound, a halogen-substituted carbonate-based compound, a sultone-based compound, a sulfate-based compound, a phosphate-based or phosphite-based compound, a borate-based compound, a nitrile-based compound, a benzene-based compound, an amine-based compound, a silane-based compound, and a lithium salt-based compound.
  • the cyclic carbonate-based compound may include vinylene carbonate (VC) or vinyl ethylene carbonate (VEC).
  • VC vinylene carbonate
  • VEC vinyl ethylene carbonate
  • the halogen-substituted carbonate-based compound may be fluoroethylene carbonate (FEC).
  • FEC fluoroethylene carbonate
  • the sultone-based compound may be at least one compound selected from the group consisting of 1,3-propane sultone (PS),1,4-butane sultone, ethane sultone, 1,3-propene sultone (PRS), 1,4-butene sultone, and 1-methyl-1,3-propenesultone.
  • PS 1,3-propane sultone
  • PRS 1,3-propene sultone
  • 1-methyl-1,3-propenesultone 1-methyl-1,3-propenesultone
  • the sulfate-based compound may be ethylene sulfate (ESa), trimethylene sulfate (TMS), or methyl trimethylene sulfate (MTMS).
  • ESa ethylene sulfate
  • TMS trimethylene sulfate
  • MTMS methyl trimethylene sulfate
  • the phosphate-based or phosphite-based compound may be at least one compound selected from the group consisting of lithium difluoro(bisoxalato)phosphate, lithium difluorophosphate,tris(trimethylsilyl)phosphate,tris(trimethylsi lyl)phosphite, tris(2,2,2-trifluoroethyl)phosphate, and tris(trifluoroethyl)phosphite.
  • the borate-based compound may include tetraphenylborate, and lithium oxalyldifluoroborate(LiODFB) or lithium bis(oxalato)borate(LiB(C 2 O 4 ) 2 ,LiBOB).
  • the nitrile-based compound may, for example, be at least one compound selected from the group consisting of succinonitrile(SN), adiponitrile, acetonitrile, propionitrile, butyronitrile, valeronitrile, caprylonitrile, heptanenitrile, cyclopentanecarbonitrile, cyclohexanecarbonitrile, 2-fluorobenzonitrile, 4-fluorobenzonitrile, difluorobenzonitrile, trifluorobenzonitrile, phenylacetonitrile, 2-fluorophenylacetonitrile, and 4-fluorophenylacetonitrile.
  • succinonitrile(SN) succinonitrile
  • adiponitrile acetonitrile
  • propionitrile propionitrile
  • butyronitrile valeronitrile
  • caprylonitrile caprylonitrile
  • heptanenitrile cyclopentanecarbonitrile
  • the benzene-based compound may be fluorobenzene
  • the amine-based compound may be triethanolamine or ethylenediamine
  • the silane-based compound may be tetravinylsilane.
  • the lithium salt-based compound is a compound different from the lithium salt included in the non-aqueous electrolyte solution, wherein the lithium salt-based compound may include lithium difluorophosphate (LiPO 2 F 2 ) or LiBF 4 .
  • Two or more compounds may be mixed and used as the other additives, and the total content of the compound represented by Formula 1 and other additives may be included in an amount of 50 wt% or less, specifically 0.05 to 20 wt%, specifically 0.05 to 10 wt%, based on the total weight of the non-aqueous electrolyte solution.
  • the amount of the other additives satisfies the above range, the low-temperature output characteristics of the battery may be improved and high-temperature storage characteristics and high-temperature lifespan characteristics may be more effectively improved. The occurrence of battery side reactions caused by the remaining additives after the reaction may be also prevented.
  • a lithium secondary battery including the non-aqueous electrolyte solution for a lithium secondary battery of the present invention.
  • the lithium secondary battery may include a positive electrode including a positive electrode active material, a negative electrode including a negative electrode active material, a separator disposed between the positive electrode and the negative electrode, and the above-described non-aqueous electrolyte solution for a lithium secondary battery.
  • the lithium secondary battery of the present invention may be prepared by injecting the non-aqueous electrolyte solution of the present invention.
  • the lithium secondary battery of the present invention may be prepared according to a conventional method known in the art and used, and a method of preparing the lithium secondary battery of the present invention is specifically the same as that described later.
  • the positive electrode according to the present invention may include a positive electrode active material layer including a positive electrode active material, and, if necessary, the positive electrode active material layer may further include a conductive agent and/or a binder.
  • a lithium transition metal oxide including lithium and at least one metal selected from cobalt, manganese, nickel, or aluminum and may specifically include at least one of a lithium-manganese-based oxide, a lithium iron phosphate and a lithium-nickel-manganese-cobalt-based oxide (
  • the lithium-manganese-based oxide may be LiMnO 2 or LiMn 2 O 4
  • the lithium iron phosphate may be LiFePO 4 .
  • the lithium-nickel-manganese-cobalt-based oxide may include at least one selected from the group consisting of Li(Ni 1/3 Mn 1/3 Co 1/3 )O 2 , Li(Ni 0.6 Mn 0.2 Co 0.2 )O 2 , Li(Ni 0.5 Mn 0.3 Co 0.2 )O 2 , Li(Ni 0.7 Mn 0.15 Co 0.15 )O 2 and Li(Ni 0.8 Mn 0.1 Co 0.1 )O 2 ,and it is desirable to include a transition metal oxide in which a nickel content is 60 atm% or more. That is, higher capacity may be achieved as an amount of the nickel among the transition metals is increased.
  • Such lithium complex oxide may be at least one selected from the group consisting of Li(Ni 0.6 Mn 0.2 Co 0.2 )O 2 , Li(Ni 0.7 Mn 0.15 Co 0.15 )O 2 and Li(Ni 0.8 Mn 0.1 Co 0.1 )O 2 .
  • the positive electrode active material may include lithium-cobalt-based oxide (e.g., LiCoO 2 , etc.), lithium-nickel-based oxide (e.g., LiNiO 2 , etc.), lithium-nickel-manganese-based oxide (e.g., LiNi 1-Y Mn Y O 2 (where 0 ⁇ Y ⁇ 1), LiMn 2-z Ni z O 4 (where 0 ⁇ Z ⁇ 2)), lithium-nickel-cobalt-based oxide (e.g., LiNi 1-Y1 Co Y1 O 2 (where 0 ⁇ Y1 ⁇ 1)), lithium-manganese-cobalt-based oxide (e.g., LiCo 1-Y2 Mn Y2 O 2 (where 0 ⁇ Y2 ⁇ 1), LiMn 2-Z1 Co Z1 O 4 (where 0 ⁇ Z1 ⁇ 2)), lithium-nickel-manganese-cobalt-based oxide (e.g., Li(Ni p1 Co), LiNi 1-Y Mn Y
  • the positive electrode active material may be present in an amount of 90 wt% to 99 wt%, specifically, 93 wt% to 98 wt% based on a total weight of solid content in the positive electrode active material layer.
  • the conductive agent is not particularly limited as long as it has conductivity without causing chemical changes in the battery, and for example, a conductive material such as carbon powder such as carbon black, acetylene black, Ketjen black, channel black, furnace black, lamp black, or thermal black; graphite powder such as natural graphite with a well-developed crystal structure, artificial graphite, or graphite; conductive fibers such as carbon fibers or metal fibers; conductive powder such as fluorocarbon powder, aluminum powder, and nickel powder; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxide such as titanium oxide; or polyphenylene derivatives, may be used.
  • a conductive material such as carbon powder such as carbon black, acetylene black, Ketjen black, channel black, furnace black, lamp black, or thermal black
  • graphite powder such as natural graphite with a well-developed crystal structure, artificial graphite, or graphite
  • conductive fibers such as carbon fibers or metal fibers
  • conductive powder
  • the conductive agent is generally included in an amount of 1 to 30wt% based on the total weight of the solid content in the positive electrode active material layer.
  • the binder is a component that assists in the binding between positive electrode active material particles and in the binding between the positive electrode active material and the current collector, wherein the binder is commonly added in an amount of 1 wt% to 30 wt% based on the total weight of the solid content in the positive electrode active material layer.
  • the binder may be a fluorine resin-based binder including polyvinylidene fluoride (PVDF) or polytetrafluoroethylene (PTFE); a rubber-based binder including a styrene butadiene rubber (SBR), an acrylonitrile-butadiene rubber, or a styrene-isoprene rubber; a cellulose-based binder including carboxymethylcellulose (CMC), starch, hydroxypropylcellulose, or regenerated cellulose; a polyalcohol-based binder including polyvinyl alcohol; a polyolefin-based binder including polyethylene or polypropylene; a polyimide-based binder; a polyester-based binder; and a silane-based binder.
  • PVDF polyvinylidene fluoride
  • PTFE polytetrafluoroethylene
  • a rubber-based binder including a styrene butadiene rubber (SBR), an acrylon
  • the positive electrode of the present invention as described above may be prepared by a method of preparing a positive electrode which is known in the art.
  • the positive electrode may be prepared by a method in which a positive electrode collector is coated with a positive electrode slurry, which is prepared by dissolving or dispersing the positive electrode active material, the binder, and/or the conductive agent in a solvent and then dried and rolled to form a positive electrode active material layer, or may be prepared by casting the positive electrode active material layer on a separate support, and then laminating a film separated from the support on the positive electrode collector.
  • the positive electrode collector is not particularly limited as long as it has conductivity without causing adverse chemical changes in the battery, and, for example, stainless steel, aluminum, nickel, titanium, fired carbon, or aluminum or stainless steel that is surface-treated with one of carbon, nickel, titanium, silver, or the like may be used.
  • the solvent may include organic solvents such as NMP(N-methyl-2-pyrrolidone), etc., and may be used in an amount such that desirable viscosity is obtained when the positive electrode active material as well as optionally the binder and the conductive agent are included.
  • organic solvents such as NMP(N-methyl-2-pyrrolidone), etc.
  • it may be included so that the solid content concentration in the active material slurry including the positive electrode active material and optionally the binder and the conductive material is in the range of 10 wt% to 70 wt%, preferably 20 wt% to 60 wt%.
  • the negative electrode according to the present invention includes a negative electrode active material layer including a negative electrode active material, and the negative electrode active material layer may further include a conductive agent and/or a binder, if necessary.
  • the negative electrode active material may include at least one selected from the group consisting of a carbon material capable of reversibly intercalating/deintercalating lithium ions, metal or an alloy of lithium and the metal, a metal composite oxide, a material which may be doped and undoped with lithium, and a transition metal oxide.
  • a carbon-based negative electrode active material generally used in a lithium ion secondary battery may be used without particular limitation, and, as a typical example, crystalline carbon, amorphous carbon, or both thereof may be used.
  • the crystalline carbon may be graphite such as irregular, planar, flaky, spherical, or fibrous natural graphite or artificial graphite
  • examples of the amorphous carbon may be soft carbon (low-temperature sintered carbon) or hard carbon, mesophase pitch carbide, and fired cokes.
  • a metal selected from the group consisting of Cu, Ni, Na, K, Rb, Cs, Fr, Be, Mg, Ca, Sr, Si, Sb, Pb, In, Zn, Ba, Ra, Ge, Al and Sn or an alloy of lithium and the metal may be used.
  • the material which may be doped and undoped with the lithium, may include Si, SiO x (0 ⁇ x ⁇ 2), a Si-Y alloy (where the Y is an element selected from the group consisting of alkali metal, alkaline earth metal, a Group 13 element, a Group 14 element, transition metal, a rare earth element, and a combination thereof, and is not Si), Sn, SnO 2 , and Sn-Y (where the Y is an element selected from the group consisting of alkali metal, alkaline earth metal, a Group 13 element, a Group 14 element, transition metal, a rare earth element, and a combination thereof, and is not Sn), and a mixture of SiO 2 and at least one thereof may also be used.
  • the element Y may be selected from the group consisting of Mg, Ca, Sr, Ba, Ra, Sc, Y, Ti, Zr, Hf, Rf, V, Nb, Ta, Db, Cr, Mo, W, Sg, Tc, Re, Bh, Fe, Pb, Ru, Os, Hs, Rh, Ir, Pd, Pt, Cu, Ag, Au, Zn, Cd, B, Al, Ga, Sn, In, Ge, P, As, Sb, Bi, S, Se, Te, Po, and a combination thereof.
  • the transition metal oxide may include lithium-containing titanium composite oxide (LTO), vanadium oxide, and lithium vanadium oxide.
  • LTO lithium-containing titanium composite oxide
  • vanadium oxide vanadium oxide
  • lithium vanadium oxide lithium vanadium oxide
  • the negative electrode active material may be present in an amount of 80 wt% to 99 wt% based on a total weight of the solid content in the negative electrode active material layer.
  • the conductive agent is a component for further improving the conductivity of the negative electrode active material, wherein the conductive agent may be added in an amount of 1 wt% to 20 wt% based on the total weight of the solid content in the negative electrode active material layer.
  • Any conductive agent may be used without particular limitation so long as it has conductivity without causing adverse chemical changes in the battery, and, for example, a conductive material such as: graphite powder such as natural graphite and artificial graphite; carbon black such as acetylene black, Ketjen black, channel black, furnace black, lamp black, and thermal black; conductive fibers such as carbon fibers and metal fibers; conductive powder such as fluorocarbon powder, aluminum powder, or nickel powder; conductive whiskers such as zinc oxide and potassium titanate; conductive metal oxide such as titanium oxide; or polyphenylene derivatives, may be used.
  • the binder is a component that assists in the binding between the conductive agent, the active material, and the current collector, wherein the binder is commonly added in an amount of 1wt% to 30wt% based on the total weight of the solid content in the negative electrode active material layer.
  • the binder may be a fluorine resin-based binder including polyvinylidene fluoride (PVDF) or polytetrafluoroethylene (PTFE); a rubber-based binder including a styrene-butadiene rubber (SBR), an acrylonitrile-butadiene rubber, or a styrene-isoprene rubber; a cellulose-based binder including carboxymethylcellulose (CMC), starch, hydroxypropylcellulose, or regenerated cellulose; a polyalcohol-based binder such as polyvinyl alcohol; a polyolefin-based binder including polyethylene or polypropylene; a polyimide-based binder; a polyester-based binder; and a silane-based binder.
  • PVDF polyvinylidene fluoride
  • PTFE polytetrafluoroethylene
  • SBR styrene-butadiene rubber
  • CMC carboxymethylcellulose
  • the negative electrode may be prepared by a method of preparing a negative electrode which is known in the art.
  • the negative electrode may be prepared by a method in which a negative electrode collector is coated with a negative electrode slurry, which is prepared by dissolving or dispersing the negative electrode active material as well as selectively the binder and the conductive agent in a solvent, rolled and dried to form a negative electrode active material layer, or may be prepared by casting the negative electrode active material layer on a separate support and then laminating a film separated from the support on the negative electrode collector.
  • the negative electrode collector may typically have a thickness of 3 um to 500 um.
  • the negative electrode collector is not particularly limited as long as it has high conductivity without causing adverse chemical changes in the battery, and, for example, copper, stainless steel, aluminum, nickel, titanium, fired carbon, copper or stainless steel that is surface-treated with one of carbon, nickel, titanium, silver, or the like, and an aluminum-cadmium alloy may be used. Similar to the positive electrode collector, microscopic irregularities may be formed on the surface of the collector to improve the adhesion of the negative electrode active material.
  • the negative electrode collector for example, may be used in various shapes such as that of a film, a sheet, a foil, a net, a porous body, a foam body, a non-woven fabric body, and the like.
  • the solvent may include water or an organic solvent such as NMP and alcohol, and may be used in an amount such that desirable viscosity is obtained when the negative electrode active material as well as optionally the binder and the conductive agent are included.
  • the solvent may be included in an amount such that a concentration of the solid content in the negative electrode slurry including the negative electrode active material as well as optionally the binder and the conductive agent is in a range of 50 wt% to 75 wt%, preferably 50 wt% to 65wt%.
  • the lithium secondary battery according to the present invention includes a separator between the positive electrode and the negative electrode.
  • any separator may be used without particular limitation as long as it is typically used as the separator in a lithium secondary battery, and particularly, a separator having high moisture-retention ability for an electrolyte due to low resistance to the transfer of electrolyte ions may be desirable.
  • a porous polymer film generally used, for example, a porous polymer film prepared from a polyolefin-based polymer, such as an ethylene homopolymer, a propylene homopolymer, an ethylene/butene copolymer, an ethylene/hexene copolymer, and an ethylene/methacrylate copolymer, or a laminated structure of two layers or more of these may be used.
  • a porous polymer film prepared from a polyolefin-based polymer, such as an ethylene homopolymer, a propylene homopolymer, an ethylene/butene copolymer, an ethylene/hexene copolymer, and an ethylene/methacrylate copolymer, or a laminated structure of two layers or more of these may be used.
  • the lithium secondary battery according to the present invention as described above may be suitably used in portable devices, such as mobile phones, notebook computers, and digital cameras, and electric cars such as hybrid electric vehicles (HEVs).
  • portable devices such as mobile phones, notebook computers, and digital cameras
  • electric cars such as hybrid electric vehicles (HEVs).
  • HEVs hybrid electric vehicles
  • a battery module including the lithium secondary battery as a unit cell and a battery pack including the battery module are provided.
  • the battery module or the battery pack may be used as a power source of at least one medium and large sized device of a power tool; electric cars including an electric vehicle (EV), a hybrid electric vehicle, and a plug-in hybrid electric vehicle (PHEV); or a power storage system.
  • electric cars including an electric vehicle (EV), a hybrid electric vehicle, and a plug-in hybrid electric vehicle (PHEV); or a power storage system.
  • a shape of the lithium secondary battery of the present invention is not particularly limited, but a cylindrical type using a can, a prismatic type, a pouch type, or a coin type may be used.
  • the lithium secondary battery according to the present invention may not only be used in a battery cell that is used as a power source of a small device, but may also be used as a unit cell in a medium and large sized battery module including a plurality of battery cells.
  • LiPF 6 was dissolved in a non-aqueous organic solvent, in which ethylene carbonate (EC), propylene carbonate (PC), ethyl propionate (EP) and propyl propionate (PP) were mixed in a volume ratio of 20:10:20:50, such that a concentration of the LiPF 6 was 1.0 M
  • a non-aqueous electrolyte solution was prepared by adding 0.1 wt% of a compound represented by Formula 1a, and 0.5 wt% of vinylene carbonate (hereinafter "VC"), 1.0 wt% of 1,3-propanesultone (hereinafter "PS”), 5.0 wt% of fluoroethylene carbonate (hereinafter “FEC”), 1.0 wt% of succinonitrile (hereinafter “SN”) and 0.5 wt% of lithium oxalyldifluoroborate (hereinafter "LiODFB”) as other additives (see Table 1 below).
  • VC vinylene carbonate
  • a positive electrode active material particle LiCoO 2
  • a conductive agent carbon black
  • a binder polyvinylidene fluoride
  • NMP N-methyl-2-pyrrolidone
  • a positive electrode collector Al thin film with a thickness of 15 um was coated with the positive electrode slurry, dried, and then roll-pressed to prepare a positive electrode.
  • a negative electrode active material graphite
  • a binder SBR-CMC
  • a conductive agent carbon black
  • a negative electrode collector Cu thin film with a thickness of 6um, was coated with the negative electrode slurry, dried, and then roll-pressed to prepare a negative electrode.
  • An electrode assembly was prepared by sequentially stacking the positive electrode, a polyolefin-based porous separator coated with inorganic particles (Al 2 O 3 ), and the negative electrode.
  • a lithium secondary battery was prepared in the same manner as in Example 1 except that a non-aqueous electrolyte solution was prepared by adding 1.0 wt% of a compound represented by Formula 1a, and 0.5 wt% of VEC, 1.0 wt% of PS, 5.0 wt% of FEC, 1.0 wt% of SN and 0.5 wt% of LiODFB as other additives (see Table 1 below).
  • a lithium secondary battery was prepared in the same manner as in Example 1 except that a non-aqueous electrolyte solution was prepared by adding 5.0 wt% of a compound represented by Formula 1a, and 0.5 wt% of VEC, 1.0 wt% of PS, 5.0 wt% of FEC, 1.0 wt% of SN and 0.5 wt% of LiODFB as other additives (see Table 1 below).
  • a lithium secondary battery was prepared in the same manner as in Example 1 except that a non-aqueous electrolyte solution was prepared by adding 11.0 wt% of a compound represented by Formula 1a, and 0.5 wt% of VEC, 1.0 wt% of PS, 5.0 wt% of FEC, 1.0 wt% of SN and 0.5 wt% of LiODFB as other additives (see Table 1 below).
  • a lithium secondary battery was prepared in the same manner as in Example 1 except that a non-aqueous electrolyte solution was prepared by adding 1.0 wt% of a compound represented by Formula 1b, and 0.5 wt% of VEC, 1.0 wt% of PS, 5.0 wt% of FEC, 1.0 wt% of SN and 0.5 wt% of LiODFB as other additives (see Table 1 below).
  • a lithium secondary battery was prepared in the same manner as in Example 1 except that a non-aqueous electrolyte solution was prepared by adding 1.0 wt% of a compound represented by Formula 1c, and 0.5 wt% of VEC, 1.0 wt% of PS, 5.0 wt% of FEC, 1.0 wt% of SN and 0.5 wt% of LiODFB as other additives (see Table 1 below).
  • a lithium secondary battery was prepared in the same manner as in Example 1 except that a non-aqueous electrolyte solution was prepared by adding 0.5 wt% of VEC, 1.0 wt% of PS, 5.0 wt% of FEC, 1.0 wt% of SN and 0.5 wt% of LiODFB as other additives (see Table 1 below).
  • a lithium secondary battery was prepared in the same manner as in Example 1 except that a non-aqueous electrolyte solution was prepared by adding a compound represented by the following Formula 2 instead of a compound represented by Formula 1a (see Table 1 below).
  • a lithium secondary battery was prepared in the same manner as in Example 2 except that a non-aqueous electrolyte solution was prepared by adding a compound represented by the following Formula 2 instead of a compound represented by Formula 1a (see Table 1 below).
  • a non-aqueous electrolyte solution was prepared by adding a compound represented by the following Formula 2 instead of a compound represented by Formula 1a (see Table 1 below).
  • Formula 1a Lithium salt Non-aqueous organic solvent Additives Other additives Amount (wt%) Formula Amount (wt%)
  • Example 2 1a 1.0
  • Example 3 1a 5.0
  • Example 4 1a 11.0
  • Example 5 1b
  • Example 6 1c 1.0 Comparative Example 1 - - Comparative Example 2 2 0.1 Comparative Example 3 2 1.0
  • the initial interface resistance was calculated from the amount of voltage drop measured using VMP3 (manufactured by Biologics), and the results are presented in Table 2 below by expressing the same as a contrast ratio (%) with respect to the secondary battery of Comparative Example 1.
  • Capacity retention % discharge capacity after 200 cycles / discharge capacity after 1 cycle ⁇ 100 [Table 2] Room temperature (25°C) Interfacial resistance (%) Discharge Capacity (mAh) Capacity retention rate (%)
  • Example 6 -9.7 4971 96.6 Comparative Example 1 Standard 4765 92.0 Comparative Example 2 1.4 4710 90.8 Comparative Example 3 3.8 4683 88.2
  • the secondary batteries of Examples 1 to 3, 5 and 6 of the present invention improved all the interfacial resistance (%) at room temperature (25°C), discharge capacity (mAh), and capacity retention rate (%) after the 200 cycles compared to the secondary batteries of Comparative Examples 1 to 3.
  • the 2C charging potential of the secondary batteries of Examples 1 to 3, 5, and 6 at a low temperature is 4.10 V or less, and may be charged at a lower potential compared with the secondary batteries of Comparative Examples 1 to 3.
  • the 2C charging potential was lower compared with the secondary battery of Example 1, which means that the overpotential has decreased.
  • the effect of reducing resistance was more improved when the additive content was 1.0 wt% compared to when the additive content is 0.1 wt%.

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EP22881277.2A 2021-10-12 2022-10-06 Électrolyte non aqueux pour batterie secondaire au lithium et batterie secondaire au lithium le comprenant Pending EP4287339A1 (fr)

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